Optical Isomerism and Chiral Molecules.

1. What are enantiomers? [1]

2. The amino acid glycine (R = H) does not exhibit optical isomerism. Explain
why? [1]
3. Draw the optical isomers of CH3CH(OH)CN. [2]
4. Identify the chiral centres in the following molecules:
(a) CH3CH(NH2)COOH (b) C(CH3CH2)C6H8CH3 [bolded part is benzene
ring] [2]
5. Which of the following molecules exhibit optical isomerism?
(a) Butan-2-ol [1]
(b) 2-chloromethylpropane [1]
(c) 2,3-dihydroxypropanal [1]
(d) 3-bromopentane [1]
(e) 1-chloro-3-methylpentane [1]
(f) 2-methylbutanoic acid. [1]
Examination Practice Questions
Tyrosine and threonine are two acids used in the construction of proteins. Their R
groups both contain hydroxyl groups. Their structures are shown below.

1. State how the hydroxyl groups are different in tyrosine and threonine and give a
chemical test to distinguish between them. Describe what you would see in each
case. [4]
2. Tyrosine and threonine are chiral molecules. Identify all of the chiral carbon atoms
in each structure. [2]
3. Threonine can form a condensation polymer containing amine side chains. Draw
the repeating unit for this polymer and give the name of the link joining the monomer
units together.
[2]
4. In foodstuffs such as cheese, tyrosine decays into
tyramine. Tyramine is possibly responsible for migraine-type
headaches.
Draw the table below and show the structures of the products formed
when tyramine reacts with the named reagents. [5]
reagent Products(s) formed
Hydrochloric acid
Ethanoyl chloride

5. Although tyramine is not very soluble in water it will dissolve if a little aqueous
alkali is added to a mixture of tyramine and water. Explain why tyramine is able to
do this. [2]